June 2007

So Many Problems, So Little Time
Dear Jane,

My problem…well, my problems, plural…they tend to vary and I would appreciate your feedback, Jane.

First, my virginity. This is something that pains me to no end. Simply put, I’m a nearly 27 years old and still a virgin. In a day and age when it’s routine for kids to have sex for the first time in their mid to late teens, I’m well beyond that point and year by year creeping closer to 30.

Is this something I should kick myself over? I ask because I constantly do so. It hurts…it’s shameful and I fear very, very few women would even give me a chance, based only on the fact that I’m a virgin.

Onto part two: confidence. This is something that I simply don’t have and have no idea how to jumpstart. It may be in large part because I’ve also been a longtime victim of clinical depression. I would imagine these two things, the lack of confidence and the depression would go hand in hand. Any ideas to counter these things?

Onto part three of my inquiry. Penis size…yeah I know another penis question. I’m right at four inches and honestly get off on the fantasy of having a Dominant Woman and her friends poke fun at and shame me because of it. At the same time I sometimes get 'too' into the fantasy and it depresses me just as much as it turns me on. Not sure if that even makes sense, but something that brings me so much joy, also brings me so much pain. How would a person find a nice middle ground? Something that would allow them to cherish the humiliation of having a small tool, yet not allow it to make them even more depressed?

Finally parts four and five of my question. I’ve long had a thing for cross-dressing. I’ve been dressing for all but five or six years of my life and though I've tried to shake it on numerous times, going so far as to throw away years and years of makeup and clothing I’ve accumulated, it always comes back. This is something else I worry about. It’s clear at this point that I can’t not dress up. I say this knowing that any girl I was with long enough would eventually find out and this excites the humiliation junkie side of me, but scares the side longing for companionship, because I know this would be enough to scare a lot of females off. Is this fear a valid one?

Last and not least, I’ve always classified myself as being straight. However, of late I’ve had recurring gay fantasies (mostly dealing with being forced by a dom to suck off her “real man”).

I’m seriously starting to think I may be bisexual. Would this final fantasy lead you to believe that to be the case? Or is this fantasy not enough to lead one to form an opinion either way? I’m honestly confused about my sexuality…is there a tiny piece of me inside that doesn’t want to admit that I’m into men sexually?

Sorry for being so long winded and would again appreciate your viewpoints. Keep up the good work.

My Confused Darling,

Problems? What problems? Where you see problems, I see vast opportunity to explore and have fun with the sexual gifts you’ve been given. It’s all about perception.

Based on your description of yourself, sweetie, I’d think twice before answering a “personals” ad, for I fear it would read: “You wouldn’t want to give me a chance because I’m almost 30 and still a virgin. I lack self-confidence and have clinical depression, too. My small penis only adds to my depression, because it’s wrong for me to be excited by the idea of a woman erotically humiliating me for it. Also, unfortunately, I’ve tried but cannot give up cross-dressing. And I’m starting to wonder whether I’m gay because I have fantasies of being forced by a woman to perform orally on a man.”

May I take the liberty to characterize you in a different light? “I’m an almost-thirty-year-old man saving myself for a very special woman. This lucky woman will be graced with my adoration and fertile imagination in a relationship of true equals. I seek a sexually sophisticated woman who understands the power of dominating a man sexually and appreciates the shared richness of acting out fantasy. If you are that woman, you will appreciate my responsiveness to erotic humiliation and teasing coupled with my giving nature. I believe fantasy—yours, mine, and that which we create together—is a conduit to passion and growth of a very special connection. Reply to this ad only if you possess open-mindedness, a loving heart, and sense of adventure.”

See the difference, sweetheart? It’s all in perception. Why call something a “problem” when you can just as easily see it as an opportunity for exploration and deep connection? In the revised version of the ad, I needn’t mention cross-dressing, small-penis teasing, or forced fellatio because these are specifics that lie under the big tent of “sexual submission.” And the ad effectively addresses your desire to be dominated very clearly. HOW that’s achieved may include but need not be limited to cross-dressing, small-penis teasing, and forced fellatio.

On to specifics: Get to a doc and find a workable medication to treat your depression. Exercise daily to increase your endorphin level. To get over the label of “virgin” that you so hate, hire a pro to deflower you; be sure you request a woman who’s pretty, around your age, and who knows in advance that this is your first time.

Subscribe to David DeAngelo’s newsletter online. This man’s a genius when it comes to building self-confidence, particularly as it pertains to relating to women. He even deals with depression in his “Inner Game” program.

Join Janus, People Exchanging Power, and any other organizations in your area focused on sexual exploration.

Please do what’s necessary—therapy, reading, meditation—to embark on a journey of self-acceptance, with a goal of self-celebration. Tune out nay-sayers who judge sexuality that lies in the creative space you inhabit, chant affirmations as you exercise, and think of your body as a gift to be enjoyed in all ways. You are an alive, sensuous, sexual creature of great creativity and curiosity.

Whether you are gay or straight is less important than believing you’re “worth it” and mustering courage to explore. And, by the way, that you wish to be “forced” by a woman to perform orally on a man is more an indication of your wishing to be dominated than of bisexuality. Not that it really matters; sexual orientation exists on a continuum and can change over our lifetime. Whatever yours is, it’s meant to be enjoyed.

Good luck, baby boy. Write and let me know how it goes. And right now, as of this moment, unlock the cage you keep yourself in and promise me you’ll eliminate the word “problems” from your vocabulary. For, if you embrace yourself in all your beautiful sexual complexity, you’ll find untold ecstasy.

He Loves his Wife but T-Girls Scratch His Itch
Dear Jane,

I am 26 years old. I got married last June; before that I was with my wife for about 3 years. I cheated on her many times with t-girls. I have been aroused by men who look like women since I was 17 or 18. I had my first sexual encounter with a transsexual when I was 21. We had a boyfriend-girlfriend thing for about a year and then called it quits because she lived about an hour away and the long distance thing just didn’t work.

Ever since then I have craved cock but not just any cock. I don’t like regular guys; I prefer t-girls or some passable cross-dressers. However, I love my wife so much…I don’t know what to do about it.

When my wife and I first got together we had sex like jackrabbits. I used to eat her pussy all the time and I loved sucking on her toes (she has a very sexy size 5 feet). I’d please her, then do it to her doggy-style, which she prefers. Then I’d flip her over onto her back and tell her to suck my nipples. I’d think of a t-girl banging me in my tight ass and I’d cum in no time. Why is it I need that kind of stuff to get my nut off while I’m supposed to be making love with my wife?

My wife is great. She cooks for me and cleans for me and we get along well. In the beginning I told her about my past relationships and she was okay with them. We even went to a sex store and bought a strap-on. We used it one time, but I prefer the real thing, which my wife refuses to consider.

Now our sex life is nil and she tells me I’m a faggot (am I?). We used to talk about me sucking on a t-girl’s cock and getting banged in the ass, then we’d have some real hot sex but now she doesn’t even want to talk about it. She still lets me get my Transformation magazine in the mail, that’s about it. Do you have any advice for me, Jane?

Stuck Between Two Kinds of Women

My Darling Stuck,

If we didn’t have social constructs about what a “normal” relationship looks like, you’d probably be happily settled down with a wonderful t-girl. As it is, you appear to be trying to fit your round self into a square hole, struggling“in vain”to be fulfilled by a genetic woman when what you want is a woman with a little something extra (or a big something extra).

The best you can say about your wife is that she cooks and cleans for you? Ahem, you can hire those things out. She sounds verbally abusive“at the very least, disrespectful”to me. Is this the relationship you want…or do you stay because you won’t be satisfied with any genetic woman and you know it.

You wonder whether you’re gay. Well, it appears to me that you like the best of both worlds…that gorgeous hard cock AND the softness and femininity that a woman is. Whether this is “gay” or not is, to me, not answerable. Another sexologist would say that if a man likes cock, he’s gay, period. I think the glorious mystery of sexuality makes it a far more complex issue.

Anyway, our sexuality exists on a continuum—and it’s fluid, able to change over time. I think the label is far less important than being true to yourself. Only you can measure your needs and desires against society’s expectations of how we “should” behave in our private lives. Such a shame it is that the person who puts the wind in our sails isn’t always the same one on whom “everyone” puts the stamp of approval. Good luck, sweetie.

If Only His Wife Would Cooperate With His Fantasy
Dear Jane,

I have a strong, strong desire to have my wife have sex with other men while I watch or join in. I have even written stories about her and other men that I keep hidden on my computer.

I have spoken with her about this and sometimes when we are having sex if I say some thing she will say you never know what will happen and other times she will just say no way.

I set her up with a man one night several years back. I bought tickets to a rock concert we both wanted to go to. Well, a week before the concert I told her I could not make it and told her to find someone to go with. I told her to make sure it was a guy for security reasons. She asked her best friend’s brother.

I even got her a motel room and they went to the concert together and stayed in the motel together but did not do anything. He tried…but nothing happened. I know because I had my ear to the wall in the next room.

I want this fantasy to come true in the worst way, Jane. I want it to either go away or acted out so that I can be satisfied and leave it behind.

I don’t even care who she’s with; I guess I prefer a guy with a huge cock but I’ll take anyone.

When we first got together I asked her to sleep with my cousin and she did, but after she did it for me she did it with him behind my back—which is NOT the idea.

I feel like I’m going crazy. All I have now is the stories I write about it.

Need Satisfaction

Darling,

You need more than satisfaction. You need to wrap your mind around the idea of consensual sex. Your wife doesn’t want to sleep with other men, at least while you watch.

You say that if your wife would have sex with another man just one time you’d be satisfied, but you won’t be. Didn’t work when she was with your cousin, did it? Fantasies are not momentary pleasures, like our favorite TV shows that we can turn on and off at will. Fantasies are shows we replay over and over and over again. We might be willing to let go of their plot line…but their plot line will never let go of us.

Get pornography depicting the scenario you want and continue to write your own fantasies. And, please, horny guy, try to focus on your wife’s needs and desires. I have the feeling you’ve never even asked her what she wants. Why don’t you do that for her, baby? When you replace whining with giving, you may be surprised by all she’ll give you in return.

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